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Volume 69 
Part 6 
Page o844  
June 2013  

Received 24 April 2013
Accepted 2 May 2013
Online 11 May 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.002 Å
R = 0.049
wR = 0.161
Data-to-parameter ratio = 13.0
Details
Open access

3-Amino-5,6-dimethyl-1,2,4-triazin-2-ium nitrate

aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna, Tunisie,bDepartment of Chemical and Pharmaceutical Sciences, Centre for Structural Diffractometry, University of Ferrara, Via L. Borsari 46, I-44121 Ferrara, Italy, and cLaboratoire de Chimie Organométallique de Surface (LCOMS), Ecole Superiéure de Chimie Physique Electronique, Villeurbanne Cedex, France
Correspondence e-mail: cherif_bennasr@yahoo.fr

In the title compound, C5H9N4+·NO3-, the organic cations and the nitrate anions have both crystallographically imposed mirror symmetry and are linked via N-H...O hydrogen bonds, forming infinite chains running along the c-axis direction. The values of the N-O bond lengths [1.2256 (19)-1.2642 (18) Å] and O-N-O angles [118.39 (16)-121.64 (15)°] indicate that the nitrate anion exhibits a slightly distorted C3h geometry. The N atom of the NH2 group has sp2 character.

Related literature

For general background to hybrid materials, see: Benali-Cherif et al. (2007[Benali-Cherif, N., Kateb, A., Boussekine, H., Boutobba, Z. & Messai, A. (2007). Acta Cryst. E63, o3251.]); Messai et al. (2009[Messai, A., Direm, A., Benali-Cherif, N., Luneau, D. & Jeanneau, E. (2009). Acta Cryst. E65, o460.]). For studies of amine salts, see: Jayaraman et al. (2002[Jayaraman, K., Choudhury, A. & Rao, C. N. R. (2002). Solid State Sci. 4, 413-422.]); Steiner (2002[Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48-76.]). For related structures, see: Gilli et al. (1994[Gilli, P., Bertolasi, V., Ferretti, V. & Gilli, G. (1994). J. Am. Chem. Soc. 116, 909-915.]); Boenigk & Mootz (1988[Boenigk, D. & Mootz, D. (1988). J. Am. Chem. Soc. 110, 2135-2139.]); Jin et al. (2001[Jin, Z. M., Pan, Y. J., Hu, M. L. & Shen, L. (2001). J. Chem. Crystallogr. 31, 191-195.]).

[Scheme 1]

Experimental

Crystal data
  • C5H9N4+·NO3-

  • Mr = 187.17

  • Orthorhombic, P n m a

  • a = 19.7213 (2) Å

  • b = 6.4245 (2) Å

  • c = 6.7197 (6) Å

  • V = 851.38 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 295 K

  • 0.32 × 0.18 × 0.12 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 2321 measured reflections

  • 1326 independent reflections

  • 1031 reflections with I > 2[sigma](I)

  • Rint = 0.014

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.161

  • S = 1.04

  • 1326 reflections

  • 102 parameters

  • All H-atom parameters refined

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3N...O1 0.98 (4) 1.79 (4) 2.770 (2) 178 (3)
N4-H1N...O2 0.97 (3) 1.93 (3) 2.898 (2) 166 (3)
N4-H2N...O1i 0.87 (4) 2.18 (4) 3.043 (2) 173 (3)
Symmetry code: (i) x, y, z+1.

Data collection: KappaCCD Server Software (Nonius, 1997[Nonius (1997). KappaCCD Server Software. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEP-III, Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5062 ).


Acknowledgements

We would like to acknowledge the support provided by the Secretary of State for Scientific Research and Technology of Tunisia.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Benali-Cherif, N., Kateb, A., Boussekine, H., Boutobba, Z. & Messai, A. (2007). Acta Cryst. E63, o3251.  [CSD] [CrossRef] [details]
Boenigk, D. & Mootz, D. (1988). J. Am. Chem. Soc. 110, 2135-2139.  [CrossRef] [ChemPort] [ISI]
Burnett, M. N. & Johnson, C. K. (1996). ORTEP-III, Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gilli, P., Bertolasi, V., Ferretti, V. & Gilli, G. (1994). J. Am. Chem. Soc. 116, 909-915.  [CrossRef] [ChemPort] [ISI]
Jayaraman, K., Choudhury, A. & Rao, C. N. R. (2002). Solid State Sci. 4, 413-422.  [ISI] [CSD] [CrossRef] [ChemPort]
Jin, Z. M., Pan, Y. J., Hu, M. L. & Shen, L. (2001). J. Chem. Crystallogr. 31, 191-195.  [ISI] [CSD] [CrossRef] [ChemPort]
Messai, A., Direm, A., Benali-Cherif, N., Luneau, D. & Jeanneau, E. (2009). Acta Cryst. E65, o460.  [CSD] [CrossRef] [details]
Nonius (1997). KappaCCD Server Software. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48-76.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o844  [ doi:10.1107/S1600536813012026 ]

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